Hiccup and Toothless vs Ash and Charizard
by Stevethebarbarian
Summary: Who cares if the reasons for fighting are stupid, let's have a fight! When Hiccup and Toothless take on Pokemon's iconic human/dragon duo, who will come out on top? Rated T for some pretty nasty violence, and major character death. Yeah, one of the duos dies at the end. Just a warning.
"PIKACHUUUUUU! Hey, PIIIIIIKACHUUUUU! WHERE ARE YOU?"

Ash Ketchum was flying on the back of his Charizard, looking for his Pikachu, who had accidentally stowed away on a large wooden ship that had set sail from a nearby port. He coun't seem to find it in the endless sea of ice. But then, in the distance, he caught sight of smoke.

"Charizard, go there!" he said, pointing toward the plume of black smoke.

The dragon picked up the pace, moving quickly toward the burning mass, which Ash recognized as a ship. A ship that was rapidly turning to ash from a virtual bonfire on it's deck. Nearing the wreck, Ash was filled with a sense of extreme foreboding, as he realized that the ship was being raided by multiple fire-breathing dragons.

"Whoah, I don't recognize any of those pokemon," Ash said, rapidly pulling out his Pokedex, with no results.

"WOW! A bunch of new species! Wait... Pikachu!"

Charizard flew at top speeds toward the ship, as they both heard a whistling sound and saw a black object fly overhead at incredible speeds and land on the deck of the burning ship. Ash swooped down to take a closer look at the lifeboats he saw floating away from the ship and was happily suprised to see Pikachu in one of them, but before he headed in to rescue him, he decided to investigate the ship.

"What the..."

He saw a small black dragon, a masked man on it's back, raise it's head and let off a combination of a screech and a bark, and the other dragons stopped their attack, landed on the deck, bowed, and flew off.

The masked figure stepped off of the dragon's back and surveyed the ship, the fires on the deck burning down to a smoulder as the reinforced wood wasn't made to burn, even when blasted by a Monserous Nightmare's magnesium flame.

"Phew, bud, that was intense. I'm glad all of those guys got off of the ship. We'll have to send a rescue party from Berk to pick them up. I can't imagine what got into those dragons to attack this ship. He stepped below deck, which was relatively undamaged. The Dragon followed.

Ash, watching from a distance, ordered Charizard to land on the deck.

"Whoah. Who were those guys? That must have been the best trainer ever! He made all of those other pokemon stop attacking."

Meanwhile, below deck, the rider, the Dragon Master Hiccup was suprised to see multiple implements of war, dragon traps and balistas, and several machines he recognised from the battle with Drago Bludvist. Furthermore, he saw the skulls of dozens of dragons, along with their bones arrayed for sale.

"Why those...! Those...! Worthless dragon hunters! Argh!"

Hiccup pulled off his mask and stormed with the unnerved Toothless up above deck, and ran right into Ash.

"Hey, you!" Hiccup shouted, "Are you with the guys who were on this ship?"

"Uuh, yeah, I guess."

"Then you have a _lot_ of explaining to do. There was the skull of a _night fury_ down there. The people who killed it may have very well killed off the last surviving night fury other than Toothless. That means that they are going extinct!"

Toothless was quite suprised by Hiccup's rage. He wasn't usually like this."

"Well... your dragons nearly killed my pokemon! So... I CHALLENGE YOU TO A POKEMON BATTLE! I CHOOSE YOU, CHARIZARD!"

The large red dragon lumbered into veiw, and the flames on it's tail surged up. It prepared to fight. Hiccup's rage had cooled a bit with his suprise at the red-clad kid's sudden outburst, and he stepped back, putting his hand on Toothless's neck.

"Ok, bud, I don't know what's going on. How about you?"

Toothless made a movement that approximated a shrug.

"Well, I guess we have no choice but to fight."

The look on Hiccup's face had become a visage of angered determination. Ash, on the other hand, wore a determined smirk. He was gonna win, no matter what came his way.

Hiccup jumped into Toothless's saddle and the two leapt into the air, circling the duo below them. Ash had decided that he wanted to jump right into it with all of his pokemon's power to try to catch the two off-gaurd.

"Charizard, use Flamethrower!"

The red dragon let out a blast of fire that rapidly approached the Night Fury flying above. Toothless reacted quickly, wrapping his wings around his torso to avoid burns, while Hiccup's reflexes were equally fast, as he jumped out of the saddle and layed down on Toothless's back, the flames passing inches to either side of him.

"Oh, boy, this guy is flame-happy. Let's get higher, maybe we can get out of his range and he will exhaust his shot limit trying to hit us."

The duo shot to a greater altitude, avoiding the bulk of the firey attack. Charizard fired a few fireballs their way, but the two mostly avoided them, and those that did hit had little effect.

"Ok, Charizard, I guess we're taking this to the air. Use fly!"

Ash hopped on Charizard's back and the dragon labourously pulled himself into the air. Hiccup looked back and saw that they were following.

"Should've seen that coming. Allright, show 'em what you can do, bud."

The duo rapidly spun around in midair and charged directly, firing off a plasma blast in the direction of the Charizard. The bulky pokemon attempted to evade, but only made a small correction to it's course, and Ash was struck directly by the blast and was thrown off of Charizard's back. The red dragon looked back in time to see Ash fall down to the ship, splintering the wood.

"Whoah, bud, I didn't mean to hit _him!"_

Hiccup and Toothless were shocked to see Ash, his hair ruined and his clothes burned, but with no other injuries, stand up and give Charizard a thumbs-up, a signal to continue fighting without him.

"Oh, my gods, that guy is _tough!_ That shot would've nearly knocked out a dragon, it should've killed him! And call me crazy, but I don't think he was wearing any armor or anything!"

Toothless grunted in agreement. He was confused too. But now Charizard was alone in the air, and unlike Toothless, he had no need for a rider. The red dragon flew at rather high speeds toward the duo, spouting flames from it's mouth like water from a hose.

"Out of the way, bud!"

Toothless dove several yards downward before streaking back up with all of his "guns" blazing, firing several blasts at the underside of the Flame Pokemon, knocking off it's balance. As Charizard fell some distance through the air, Toothless rushed up toward him at high speeds, slashing the Pokemon slightly along the chest, drawing a bit of blood.

Ash called up from the ship- "No, Charizard! Come back down here now!"

The red dragon flew down to the ship, almost crash landing and splintering a bit of the wood. Ash leapt onto Charizard's back and led him back into the air.

"Use Fly!" Ash yelled, becoming the officially mascot of pointlessness.

As Charizard laborously climed altitude, Hiccup was trying to come up with a plan to bring down the extrememly durable duo.

"Ok, bud, we just have to hit them with everything we've got, in three..."

Toothless hovered, pointing his head down at the approaching Pokemon.

"Two..."

The Night Fury's body was tensed for movement, ready to spring into action at any second.

"One..."

Toothless breathed a bit of blue flame into his throat, preparing to fire and causing his mouth to glow.

"NOW!"

The black dragon twisted it's body and flew toward Ash and Charizard at a dive, firing off several blasts of plasma that struck the Flame Pokemon directly in the face and torso. As Hiccup and Toothless streaked past their Pokemon counterpart, Ash recovered from the shock of the blow and yelled out Charzard's next order-

"Charizard, use Dragon Breath!"

The Pokemon twisted it's neck and fired off a burst of purple energy that struck Hiccup and Toothless, causing them both pain. But the problems were just beginning. Both Hiccup and Toothless realized that they were paralyzed, and were diving straight at the water, where they would surely drown. Hiccup was having trouble doing so much as muttering one sound, but he managed to choke out his advice-

"T-tooth-less. Y-you got-gotta spread y-your wi-wings! G-get a lit-litl-little more alt-altitude!"

Toothless duly complied, trying to relax the constricting muscles of his winged "shoulders," to allow his wings to spread just a bit further. Although he only managed to get a few more inches of wingspan, it was enough to cause them to pull up a few feet and crash, not into the water, but into the ship, with a thunderous- **CRASH!**

The Night Fury and his rider crashed into the deck hard enough to cause it to suffer a huge crack and to become almost a crater. Hiccup was knocked out cold, and Toothless was sore in more places than he could count. The black dragon struggled to his feet, and stumbled over to his best friend, laying unconcious on the deck, blood flowing down his forehead from a wound suffered from the crash.

As Toothless licked Hiccup's head and pushed on him a bit, trying to wake him up, Ash and Charizard crashed into him with all their wheight, over 300 pounds driving the Night Fury straight down through the deck and onto the lower floor.

"Charizard, use Slash!"

The Flame Pokemon struck Toothless with his claws, causing blood to spray onto the inner hull of the ship.

"Use Dragon Claw!"

Charizard struck again, this time it's claws glowing with purple energy.

"Use Air Slash!"

Charizard slashed again, but this time his claws didn't come even close to Toothless. Instead, the wind whipped up by the slash followed behind the claw itself, slicing open a single deep cut into the Night Fury's torso. Toothless was knocked back into the ship with the force of the hit, further cracking the ship's durable hull.

"Use Shadow Claw!"

Finally, Charizard struck out again with his claw. This time, however, the claw was shrouded in dark energy. Toothless was hit with great force, three deep slices opening in his back. Toothless cried out in agonizing pain, and fired off a blast of plasma that hit Ash at close range, sending him flying through the air out onto the deck of the ship, and actually dealing some signifigant scratches and bruises to the freakishly durable kid.

Charizard, angered, reared up onto his hind legs and prepared to use Flare Blitz to finish the Night Fury below him, but was distracted by a voice behind him.

"Don't... You... _Dare,_ hurt my Toothless."

Hiccup stood at the hole in the deck, holding his sword, coated in flaming Monsterous Nightmare saliva. His face was a strange combination of confusion from his concussion, rage at Charizard's vicious attack on his best freind, and worry at Toothless's badly injured state.

Hiccup leapt down from the upper deck, thrusting his blade with all his might, and managing to stab his weapon several inches into the Flame Pokemon's hip, casing Charizard to roar out in pain. At this point Ash leapt down from the deck, yelling in a rage.

"Get away from Charizard you creep!"

Ash grabbed Hiccup, putting him into a chokehold. The young Viking tried to ecscape, but Ash had the strength of a professional wheightlifter, and Hiccup was simply overpowered. Meanwhile, Charizard had decided that Ash could deal with Hiccup, and had turned on Toothless yet again, as the Night Fury tried to fight back with plasma blasts.

The hits did little damage to the Flame Pokemon, which used Rock Smash, exept with the "rock" in question being the smaller dragon's head, nearly knocking Toothless unconcious. Meanwhile, Hiccup was trying to resist Ash to help Toothless.

"N-no! Toothless!"

Hiccup struggled, and grabbed his sword, striking backwards with the blade, and striking Ash hard enough to deal a slight sice to the Pokemon Trainer's cheek, drawing a bit of blood. He stabbed a couple more times to the torso, his slices only enough to cause small pinpricks from that angle, and he wasn't able to break Ash's grip.

He came up with a new plan. He swung his firey sword next to Ash's face, burning his cheek enough to make Ash yell out an "owch" and release his grip. Toothless staggered to his feet and bit down with force on Charizard's tail just as he moved to interfere, before blasting him point-blank in the face, staggering the Flame Pokemon.

Ash and Hiccup now faced off, both weaving in a circle, Hiccup's blade shining with flame, Ash's fists at the ready. Ash struck out with a few swings, smacking the Dragon Master on either side of his face, before letting out an uppercut that barely grazed the young Berkian, but sent him sprawling to the ground.

Hiccup twisted his head around to look at Toothless, who was having the worst of the hand-to-hand fighting between him and Charizard, and called out his worry.

"Hang in there bud! I'll be right with you!"

Filled with new resolution, Hiccup got to his feet and swung his sword with force, catching Ash along the arm and drawing a bit of blood, before stabbing nearly and inch and a half into his torso.

"AAh! That _hurts!"_

Ash counterattacked by punching Hiccup hard enough to knock the blade out of his hands, and then struck him a haymaker to the gut, knocking the wind out of the young warrior. Ash threw a couple more punches, making sure that Hiccup was sufficiently dazed, and finally grabbed him by the neck and raised his fist menacingly.

"Oh... no... you... don't..."

Hiccup kicked his blade up into his hands, and prepared for a killing stab, as Ash readied himelf to throw a puch that would probably break the Dragon Master's neck. Toothless and Charizard paused for a moment, realizing that both of their masters would likely be dead in moments, and Charizard, feeling he had the advantage, instantly leaped toward Ash, preparing to torch Hiccup on the spot.

Charizard was shocked to see the wounded Toothless rush by him at at least three times his speed, cock his head, and fire a blast directly into his mouth, igniting the flamable gas inside and sending him flying to the wayside, before rushing, full-force, at Ash and colliding with his with enough force to send both of them straight out of the hull of the ship into the ocean outside.

Hiccup and Charizard both rushed to the hole in the side of the boat, and caught the final glimpses of the dragon and the boy, both locked in combat and sinking underwater.

"TOOOTHLESS!" Hiccup cried out, knowing that he would almost definitely drown without him, as Charizard cried out, as if to say- "ASH!"

The dragon and the man unhesitatingly dove into the water, despite Hiccup's poor swimming skills and Charizard's risk of having his fire extinguished. They swam out in different directions, Hiccup holding his sword, still burning underwater, like a torch, as Charizard expended precious fuel by spouting a bit of flame to light his way.

They both caught sight of their respective partners, Toothless's tail seemingly a bit damaged, and Ash bleeding in several places. If Hiccup had been able to breathe, he would've cried out for his friend, but as it was, it sounded more like-

"Ththls!"

Charizard swam at Ash the same way he flew, propeling himelf with his wings, as Hiccup, nearly drowned and losing conciousness, moved toward Toothless at a much slower rate. Toothless's eyes slowly closed as he lost conciousness, and Hiccup lost ran completely out of energy as he reached him.

Meanwhile, Charizard was pulling Ash out of the water, and looked back at the duo below him. Toothless's eyes were closed and Hiccup had failed to wake him up. He reached his arms around his freind's neck and fell completely unconcious, as the waves began to push them around.

Charizard pulled the sputtering Ash out onto the ship's deck, where Ash looked down at the water, and then up at Charizard, who's flame was spouting back up after nearly going out. Charizard simply shook his head, as Ash looked back down at the rolling waves.

"Well. I guess... we're done here... I never meant for this to happen..."

Had he been there, when Hiccup finally completely lost conciousness, he would've seen the eyes of the Night Fury suddenly open.

"Ok, Charizard, let's go. Use fly..."

As Ash was hopping up onto his Pokemon's back, he was treated to a majestic sight.

 **CUE:** **Where No One Goes**

Hiccup and Toothess shot out of the water at incredible speeds, Hiccup barely able to hold on to his back, coughing out water. He opened his eyes and suddenly came to the realization that he was out of the water, on Toothless's back. They were both alive.

"YEEEEAH! Alright bud! I was so worried about you. Now. Let's end this."

Toothless needed no further prompting, and shot at Ash and Charizard at mach speeds, a whisling sound made by Toothless's wings.

"Ok, bud. NOW!"

Toothless fired off a massive blast, the impact knocking Ash through the air and blasting a hole in the ship's deck to boot. Charizard fired off his Flamethrower, but Toothless flew through it almost as if he enjoyed it, firing off more blasts at Charizard.

The Flame Pokemon was getting mad, and it leapt into the air, flying at Toothless at high speeds.

 **CUE:** **Mega Charizard X Theme**

Charizard struck Toothless with signifingant force, dropping Hiccup off of the Night Fury's back, and forcing the young Viking to use his wingsuit to land on the deck, ignite his sword, and charge at Ash while Toothess and Charizard grappled in midair.

Hiccup swung his sword at Ash, getting into a verbal argument along with his physical one.

"You almost got Toothless killed!"

Ash ducked the blow, throwing a puch of his own.

"He was attacking me! And Charizard would've died too if he had been in there a minute longer!"

Hiccup avoided the strike and stabbed with his blade.

"No you say that as if you actually _cared_ about dragons! No telling how many of those... wonderful creatures have died on this ship, and at the hands of those manning it!"

Ash caught the sword with his hands, drawling a bit of blood.

"What are you talking about! I have nothing to do with this ship"

Ash grabbed Hiccup and threw him over his shoulder, and the Dragon Master was forced to grab the railings to keep from being thrown completely off the ship.

"Absolutely. Which is exactly why you tried to kill me and Toothless right off the bat! I can't understand how Charizard has any respect for you. Actually, I can. Drago's dragons had respect for _him,_ so I really can understand."

Hiccup vaulted back onto the ship, slicing his firey blade through the air to keep his foe at bay. Meanwhile, in the sky, Toothless was having the worst of it. Charizard spammed Slash, digging deep into the Night Fury's skin each time, and followed it up with his most powerful move, the Flare Blitz. Charizard was stunned by the hit and fell to the deck of the ship, but Toothless was nearly knocked unconcious by the hit, and crashed, burning slightly, right next to Hiccup, who was distracted by the plight of his friend.

Ash took the opportunity to catch Hiccup with such a blow that he actually flew through the air to land next to Toothless. Ash figured that he had to finish things right there.

"Charizard! Use Inferno!"

The Dragon reared up and blased the duo with a massive... inferno of sheer heat, igniting the deck and Toothless's saddle, as the dragon lifted it's wings to protect the helpless Hiccup.

"T-toothless... thanks bud, you saved my life... but we can't take another of those... w-we need to get to the air.

Happy to comply and get out of the rampaging Pokemon's range, Toothless snatched up Hiccup and flew to the sky, where Charizard and Ash followed.

"Uh, oh, we're in trouble. We have to finish this quick."

The two duos charged each other. One thing was sure, neither would emerge unscathed.

 **CUE:** **Battle of the Bewilderbeast**

Charizard and Toothless both fired off fireballs, each canceling out the blasts of the other. The two dragons passed each other, their pass speed approaching 1000 miles per hour, as Toothless nicked Charizard's wing with his claws. The Flame Pokemon "walked it off," coming around for another pass, as he fired off Flamethrower long before Hiccup and Toothless came into range.

"Ok, bud, pull up. We don't want to fly into that... Bud? Pull up! PULL UP!"

As they approached the massive plume of fire at high speed, Toothless couln't manage to get a bit of altitude, as Hiccup realized that the straps that controlled the Night Fury's tail flabs had snapped, being both burned and slashed repeatedly.

"Uh oh. Deja Vu."

Hiccup realized that he couln't possibly survive the blast before him, so standing up and leaping off of Toothless, he opened his wingsuit as he called-

"Just dive, bud! You can't afford to take that!"

Toothless complied, and passed Charizard far underneath. The Night Fury cocked his head only to see that the Flame Pokemon has changed targets, and was now chasing down Hiccup. Toothless tried to turn to rescue his friend, but was unable to due to his inability to control his tail fins.

As he floundered in the air, trying to keep up his altitude and execute a full 180 turn, Charizard came ever closer to Hiccup, and the flames were seconds away from enveloping him. Toothless wasn't having it. His face clinched in a viasage of grim determination, and small spikes popped out along his back.

His wings flapped, not wildly now, but with purpose and determination. Hiccup was trying to get all the speed he cound out of his unpowered wingsuit, but Charizard was catching up nonetheless. Just as the flames began to sear Hiccup's prostetic leg, Ash and Charizard were destracted by a blast from behind, coming from the rapidly approaching Toothless.

"Toothless? Bud?! You're flying, bud! Yeah!"

In his exitement, Hiccup pumped his fist up in the air, nearly losing balance, but he wasn't going to let something like that bring him down after what they had just gone through. He preformed a massive shuttle loop, turning around to face Charizard, who was flying his way, but not paying attention. He drew his sword and...

 **SHUCK!**

Ash and Hiccup tumbled to the ground at massive speeds, Ash completely impaled by the flaming sword, and Hiccup unable to get his wingsuit back into position. Toothless realized that they were both about to crash into a rocky island, and rushed to save Hiccup.

The dragon reached them moments before the colision, and far ahead of Charizard, and bit down hard on Hiccup's mechanichal leg to catch him and stop his decent. He slowed him greatly, but inertia proved to be too great a force for the badly damaged leg to overcome, and it tore into two peices, sending Hiccup tumbling to the ground along with Ash.

Toothless cried out in horror and nearly physical pain, as he saw Hiccup hit the ground with great force and begin bleeding from a large wound in his head, and at that moment Charizard saw Ash fall to the ground with massive injuries, nearly dead. The Flame Pokemon cried out, perhaps not as anguished as Toothless, but incredibly worried as well.

The red and black dragons faced off, Toothless near Hiccup, gently nudging him as Charizard flew to Ash and looked him over, before the two beasts roared at each other with monsterous intensity. Charizard was spouting flame from his mouth and tail at copious rates, as Toothless's eyes, mouth, back, and nostrils began pulsing and glowing with blue energy.

The true match was about to begin, as Toothless reared up to fire off a massive blast, and Charizard began to initiate his Dragon Rage attack. The two fired off their blasts, and the shots canceled each other out. They each fired again. And again. And again. And again. And agian. And again. And again. Finally, Toothless began to gain the atvantage.

Hiccup staggered to his feet, blood falling from his mouth, head, and body.

"See. _This_ is what it is to earn a Dragon's loyalty. _This_ is a bond, buddy. Learn about it."

Charizard was hit by a full-force blast from Toothless, and was therefore mercifully unconcious along with Ash for what came next. The Night Fury reared up on his hind legs, spread his wings, and charged his blast for what seemed like minutes on end, before finally firing off a plasma shot that hit with such force that it blew apart both Ash and Charizard, blowing a massive hole in the flame Pokemon and tearing apart Ash from the blade and the jagged rocks that he was impaled on.

"Wow, bud. We won. Now let's get out of here before Astrid gets worried and gets everybody kidnapped again or something."

Hiccup and Toothless looked back at the scene one more time before lifting into the air, their wounds making the flight labourous. They both convinced themselves that they had no choice in the matter, but they were still seized with deep regret, and knew that they had made a mistake. But that is just life. Blow up a kid and his dragon one day, just be an average cheif the next.

"May the Valkirie look over you, and grant you peaceful entrance to Valhalla. You certainly died fighting."


End file.
